- Molecular design with silicon core: Toward commercially available hole transport materials for high-performance planar p-i-n perovskite solar cells
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Organic hole transport layers (HTL) play a very important role for realizing high performance and low-cost planar p-i-n perovskite solar cells (pero-SCs). In this work, we synthesized two X-shaped organic HTL materials, Si-OMeTPA and SiTP-OMeTPA, with silicon cores and triphenylamine (TPA) derivative branches. This molecular design strategy can substantially simplify synthetic procedures making them available for reducing device costs. This is particularly applicable for Si-OMeTPA since it can be synthesized by two steps from commercial raw materials showing a total yield of over 60%. This molecularly designed Si-OMeTPA possesses advantages of high thermal stability, high crystallinity with a long range ordered lamellar structure, and excellent hole mobility. The resulting HTL can also facilitate the sequential growth of high-quality perovskite films, giving a significantly enhanced photovoltaic performance with a best power conversion efficiency of 19.06%, which is one of the highest PCE among the planar p-i-n pero-SCs to date. In addition, the devices exhibit negligible hysteresis, good reproducibility, and stability. To the best of our knowledge, this is the first example of an easily synthesized HTL material in planar p-i-n pero-SCs that shows superior performance relative to the well-known poly(bis(4-phenyl)(2,4,6-trimethylphenyl)amine) (PTAA) HTL.
- Xue, Rongming,Zhang, Moyao,Xu, Guiying,Zhang, Jingwen,Chen, Weijie,Chen, Haiyang,Yang, Ming,Cui, Chaohua,Li, Yaowen,Li, Yongfang
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Read Online
- Element-organic frameworks with high permanent porosity
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Microporous hydrophobic polysilanes with high specific surface areas (700-1100 m2 g-1) for applications in gas adsorption are obtained using an organolithiation route. The Royal Society of Chemistry.
- Rose, Marcus,Boehlmann, Winfried,Sabo, Michal,Kaskel, Stefan
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Read Online
- Hyperbranched blue-light-emitting alternating copolymers of tetrabromoarylmethane/silane and 9,9-dihexylfluorene-2,7-diboronic acid
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The first soluble hyperbranched tetrahedral polymers were prepared by Suzuki coupling polycondensation reaction between tetrabromoarylmethane/silane and 9,9-dihexylfluorene-2,7-diboronic acid at low concentrations. The polymers exhibited high thermal stability with their decomposition temperatures (T dS) in the range 352-449°C. The polymers emitted blue light highly efficiently in both solution and the solid state. The photoluminescence quantum efficiencies of the polymers in THF solution were in the range 73-99%, and those in thin films were 38-82%. The film PL spectra of the polymers exhibited similar spectral patterns to those determined in solutions, with 1-8 nm red shift in their emission maxima and 0-8 nm increase in their full width at half-maximum (fwhm) values being observed. No long wavelength excimer-like emissions at 500-600 nm, which were typical for polyfluorenes due to their self-aggregation in the solid state, were observed. Thus, the polymers were less prone to self-aggregation in the solid state due to their hyperbranched structures. A double-layer polymer light-emitting diode (PLED) device with a configuration of ITO/P_EDOT/polymer/LiF/Ca/Ag was fabricated. The device showed bright blue emission peaking at 415 nm with an external quantum efficiency of 0.6% and a turn voltage at 6.0 V. The synthetic simplicity, good solubility and solution processability, high PL quantum efficiencies in solution and the solid state, and nonaggregating property in the solid state would make the present polymers a novel class of blue emitters.
- Liu, Xue-Ming,He, Chaobin,Hao, Xiao-Tao,Tan, Li-Wei,Li, Yanqing,Ong
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Read Online
- Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C–S/C–S Metathesis
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Porous organic materials (polymers and COFs) have shown a number of promising properties; however, the lability of their linkages often limits their robustness and can hamper downstream industrial application. Inspired by the outstanding chemical, mechanical, and thermal resistance of the 1D polymer poly(phenylene sulfide) (PPS), we have designed a new family of porous poly(aryl thioether)s, synthesized via a mild Pd-catalyzed C–S/C–S metathesis-based method, that merges the attractive features common to porous polymers and PPS in a single material. In addition, the method is highly modular, allowing to easily introduce application-oriented functionalities in the materials for a series of environmentally relevant applications including metal capture, metal sensing, and heterogeneous catalysis. Moreover, despite their extreme chemical resistance, the polymers can be easily recycled to recover the original monomers, offering an attractive perspective for their sustainable use. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new, recyclable materials.
- Morandi, Bill,Rivero-Crespo, Miguel A.,Toupalas, Georgios
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supporting information
p. 21331 - 21339
(2021/12/17)
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- Synthesis of Nanostructured Organosilicon Luminophores Based on Phenyloxazoles
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A series of nanostructured organosilicon luminophores (NOLs) composed of a central 1,4-bis(5-phenyl-1,3-oxazol-2-yl)benzene (POPOP) acceptor chromophore and various peripheral p-terphenyl and 2,5-diphenyl-1,3-oxazole donor fragments have been synthesized for the first time using van Leusen reaction and direct palladium-catalyzed C-arylation of oxazole ring. Due to different functionalities of the silicon branching centers, NOLs with different donor-acceptor ratios have been obtained. The synthesized structures are expected to possess good optical characteristics for use in photonics and optoelectronics.
- Skorotetcky,Borshchev,Cherkaev,Ponomarenko
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- Silicon-based triphenylamine derivative, preparation method thereof and application thereof in perovskite solar cell
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The invention discloses a silicon-based triphenylamine derivative, a preparation method thereof and application thereof in a perovskite solar cell. In a chemical structural formula of the silicon-based triphenylamine, substituent groups are hydrogen, methyl, methoxyl, a methylthio group and a methylseleno group, and the substituent groups can be at any substitution site of a benzene ring. The silicon-based triphenylamine derivative material is not only simple in synthesis steps and has relatively high synthetic yield, and raw material cost is extremely low, a device preparation technology is simplified after the silicon-based triphenylamine derivative material is applied to a hole transport layer of a p-i-n type planar perovskite solar cell, and conversion efficiency of the solar cell alsocan be obviously improved, so that a good application prospect is shown; besides, it is worth mentioning that the silicon-based triphenylamine derivative disclosed by the invention has good crystallinity when m is equal to 0 and is not in an amorphous form, which is infrequent in other hole transport materials, and good crystallinity after annealing is beneficial to further improvement of hole transmission rate of the silicon-based triphenylamine derivative and increase of current of the solar cell and a fill factor.
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Paragraph 0022-0023
(2018/06/16)
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- Tetrahedral Tetrakis(p-ethynylphenyl) Group IV Compounds in Microporous Polymers: Effect of Tetrel on Porosity
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Three Sonogashira–Hagihara polymerization protocols were applied for the synthesis of conjugated microporous polymers (CMPs) by using group IV tetra(p-ethynylphenyl) monomers with 1,4-diiodobenzene or 1,4-dibromobenzene. The optical properties and surface areas of the CMPs were compared and related to the preparation conditions and the geometry of the tetrahedral building block as obtained after X-ray analysis. In each series, surface areas decreased—independently from the chosen parameters of catalyst, base, and solvent—from carbon-centered CMPs (1595 m2 g?1) to silicon-, germanium-, and tin-centered (649 m2 g?1) networks.
- Uptmoor, Andrea C.,Geyer, Florian L.,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.
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p. 448 - 454
(2018/06/04)
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- COMPOUND
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The present invention relates to a compound of general formula (I) which can transport holes in an organic optoelectronic device, and to blends and solutions comprising the compound of general formula (I): wherein X is C, Si or Ge; A is a group of formula (II) wherein Z is N, P, NH, O or S; E is C1-10 alkyl or H; W is substituted or unsubstituted C5-14 aryl or substituted or unsubstituted C6-16 alkyl; e is an integer from 1 to 4; and z is 1 or 2; B, C and D are each independently A, H, C1-C12 alkyl, C5-14 aryl or OH; and a, b, c and d are each independently an integer from 1 to 5.
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Paragraph 0305-0310
(2017/06/13)
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- Three-dimensional molecular donors combined with polymeric acceptors for high performance fullerene-free organic photovoltaic devices
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Non-fullerene acceptor based organic photovoltaic devices (OPVs) reported so far are inferior to those derived from fullerenes. This increases the speculation on whether donors need to be tailored for advancing non-fullerene OPVs. We explored herein two direct arylation-derived diketopyrrolopyrrole (DPP)-based three-dimensional (3D) donors that can deliver respectable power conversion efficiencies (PCEs) of 4.64% and 4.02% with polymeric acceptor N2200 blends, surpassing those obtained from PC71BM (3.56% and 3.22%, respectively). It is found that these 3D-shaped molecular donors can yield improved photo-to-current conversion and balanced charge transport when blending with the linear N2200 polymer. This finding suggests that engineering molecular geometry can be a promising approach for developing high-performance materials.
- Liu, Shi-Yong,Jung, Jae Woong,Li, Chang-Zhi,Huang, Jiang,Zhang, Jianyuan,Chen, Hongzheng,Jen, Alex K.-Y.
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supporting information
p. 22162 - 22169
(2015/11/16)
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- A molecular breakwater-like tetrapod for organic solar cells
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We report the synthesis and characterization of a tetrapodal breakwater-like small molecule, SO, containing a tetraphenylsilane core and four cyanoester functionalized terthiophene arms. SO possesses a deep lying HOMO energy level of -5.2 eV and a narrow bandgap of 1.9 eV. Absorption, X-ray scattering and differential scanning calorimetry (DSC) measurements indicate crystalline nature of this compound but very slow crystallization kinetics. Solar cells employing SO and phenyl-C61-butyric acid methyl ester (PCBM) were fabricated and evaluated. Relatively low performance was obtained mainly due to the lack of optimal phase separation under various processing conditions including thermal annealing, slow-cooling and solvent annealing. Addition of poly(thienylene vinylene) (PTV), poly(3-hexylthiophene) (P3HT) and a platinum-containing low bandgap conjugated polymer Pt-BODIPY, into the SO/PCBM blend was found to induce device favorable phase separation and the polymers were found to act as the primary hole conductor. Such ternary blend devices showed cooperatively improved performances over binary devices employing either SO or the individual conjugated polymer alone.
- Yang, Jianzhong,He, Wenhan,Denman, Kimberly,Jiang, Ying-Bing,Qin, Yang
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p. 2108 - 2119
(2015/02/05)
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- Synthesis and characterization of di-, tri- and tetraboronic acids based on phenyl- and thienylsilane cores
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The synthesis of a series of di- tri- and tetraboronic acids based on respective phenyl- and thienylsilane cores is described. The optimal protocols involved lithiation of respective arylsilane precursors using either deprotonative lithiation or halogen/lithium exchange with n-BuLi followed by treatment of resultant intermediates with B(Oi-Pr)3 and subsequent hydrolysis, which afforded final products in good yields. X-ray crystal structures of selected diboronic derivatives were determined showing that hydrogen-bonding interactions of B(OH)2 groups are the main factor governing the supramolecular assembly.
- Gontarczyk, Krzysztof,Durka, Krzysztof,Klimkowski, Piotr,Luliński, Sergiusz,Serwatowski, Janusz,Wo?niak, Krzysztof
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- New cyano functionalized silanes: Synthesis, characterization and diphenylamine detection
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A series of novel tetrahedral silicon-centered cyano functionalized silanes, bis(4-cyanodiphenyl)dimethylsilane (1), bis(4-cyanodiphenyl) diphenylsilane (2), tri(4-cyandiphenyl)methylsilane (3), tri(4-cyandiphenyl) phenylsilane (4), and tetra(4-cyandiphenyl) silane (5), have been synthesized by Suzuki coupling reactions. They all display high thermal stability, and are fluorescent with strong emission in the region of violet to blue. Furthermore, 1-5 all exhibited the linear fluorescent quenching response to diphenylamine (DPA) with the high binding constants up to 1.0 × 106 M -1 in dichloromethane solution, demonstrating the potential application in DPA detection.
- Wang, Linlin,Wang, Dengxu,Wang, Hua,Feng, Shengyu
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- Chiral porous organic frameworks for asymmetric heterogeneous catalysis and gas chromatographic separation
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Three chiral robust diene-based porous organic frameworks (POFs) are prepared. POF-1 is shown to be an efficient heterogeneous catalyst after metallation for asymmetric conjugation addition with up to 93% ee, and it can also function as a new chiral stationary phase for gas chromatographic separation of racemates. This journal is
- Dong, Jinqiao,Liu, Yan,Cui, Yong
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supporting information
p. 14949 - 14952
(2015/01/08)
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- Tetrahedral silicon-based luminescent molecules: Synthesis and comparison of thermal and photophysical properties by various effect factors
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A series of luminescent molecules were presented employing the tetrahedral structural motif of the silicon atom, which further connected different N-containing heterocycle functional groups in their periphery using phenyl rings as the bridges. These compounds included three kinds of N-heterocycle functional silanes: imidazole derivatives (1a-h), pyrazole derivatives (2a-e) and benzimidazole derivatives (3a-b), and their structures were fully characterized by FT-IR, 1H NMR, 13C NMR and HRMS. The TGA results indicate that they all exhibit high thermal stabilities. The photophysical properties demonstrate that they are fluorescent in the violet-blue region and could be potentially applied as blue emitters for organic light-emitting diodes (OLEDs). The effect factors of sort, disposition and number of substituent groups and N-containing heterocycle functional groups on their thermal and photophysical properties were investigated. Molecular calculations were also performed to support the experimental results. Moreover, the computational results reveal that these compounds all exhibit relatively large HOMO-LUMO band gaps with the range from 4.82 eV (2d) to 5.19 eV (1a and 2c), making them become promising candidates as host materials for emitters and hole/electron blocking materials in OLEDs display.
- Wang, Dengxu,Wang, Linlin,Xue, Lei,Zhou, Debo,Feng, Shengyu,Zhao, Xian
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- Microporous cyanate resins: Synthesis, porous structure, and correlations with gas and vapor adsorptions
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Three silicon and nitrogen-centered cyanate monomers tetrakis(4- cyanatophenyl)silane, tetrakis(4-cyanatobiphenyl)silane, and tris(4-cyanatobiphenyl)amine were designedand synthesized, which were then polymerized via thermal cyclotrimerization reaction to create highly porous cyanate resin networks with systematically varied nodes and linking struts. The chemical structures of monomers and polymers were confirmed by 1H NMR, FTIR, solid-state 13C CP/MAS NMR spectra, and elemental analysis. The products are amorphous with 5% weight-loss temperatures over 428 °C. The results based on N2 and CO2 adsorption isotherms show that the pores in these polymers mainly locate in the microporous region, and the BET surface areas are up to 960 m2 g-1, which is the highest value for the porous cyanate resin reported to date. The nitrogen- and oxygen-rich characteristics of cyanate resins lead to the networks strong affinity for CO2 and thereby high CO2 adsorption capacity of 11.1 wt % at 273 K and 1.0 bar. The adsorption behaviors of H 2, CO2, benzene, n-hexane, and water vapors were investigated by correlating with the chemical composition and porosity parameters of the networks as well as the physicochemical nature of adsorbates.
- Yu, Hao,Shen, Changjiang,Tian, Mengzhe,Qu, Jing,Wang, Zhonggang
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experimental part
p. 5140 - 5150
(2012/09/22)
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- Synthesis and characterization of solution-processable highly branched iridium (III) complex cored dendrimer based on tetraphenylsilane dendron for host-free green phosphorescent organic light emitting diodes
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Solution processable highly branched iridium(III) complex fac-tris(2-phenylpyridyl)iridium-cored dendrimer based on tetraphenylsilane dendron and 2-ethylhexyloxy surface groups was prepared. The structure of dendrimer was confirmed by nuclear magnetic resonance, mass and infrared studies. Thermogravimetric analysis and differential scanning calorimetry studies show the thermal stability (T5%) of 625 K with high glass transition temperature of 423 K. Photoluminescence studies of dendrimer showed the core emission at 516 nm in solution and at 521 nm in film, indicating the highly branched non-conjugated tetrahedral tetraphenylsilane dendrons around the core highly inhibit the intermolecular interactions between the cores in the film. The solution processed green emitting phosphorescent organic light emitting diodes based on dendrimer were fabricated and characterized. The device using host free dendrimer as emitter showed the external quantum efficiency of 0.4%. The results show the potential of this new type of dendritic emitting structure in highly efficient solution processed host-free green phosphorescent organic light emitting diodes.
- Kim, Seul-Ong,Zhao, Qinghua,Thangaraju,Kim, Jang Joo,Kim, Yun-Hi,Kwon, Soon-Ki
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experimental part
p. 139 - 145
(2011/12/04)
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- New linker systems for superior immobilized catalysts
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The rigid linkers E(p-C6H4PPh2) 4 (E = Si, Sn) have been synthesized from the corresponding precursors E(p-C6H4Br)4 and immobilized by forming one (E = Si) or three (E = Sn) phosphonium groups that are attached to the silica support by electrostatic interactions. The remaining unquaternized phosphines are coordinated to Wilkinson-type Rh complexes. The catalyst immobilized by the rigid scaffold with three surface-bound phosphonium groups (E = Sn) displays superior catalytic activity and lifetime with respect to the hydrogenation of dodecene. This catalyst can be recycled 30 times in a batchwise manner under standardized conditions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Beele, Bjoern,Guenther, Johannes,Perera, Melanie,Stach, Michaela,Oeser, Thomas,Bluemel, Janet
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supporting information; experimental part
p. 2729 - 2731
(2011/02/18)
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- Tetrahedral silicon-centered imidazolyl derivatives: Promising candidates for OLEDs and fluorescence response of Ag (I) ion
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A series of novel tetrahedral silicon-centered imidazolyl derivatives, Bis(4-(imidazol-1-yl)phenyl)dimethylsilane (1), Tri(4-(imidazol-1-yl)phenyl) methyl silane (2), Bis(4-(imidazol-1-yl)phenyl)diphenylsilane (3), Tri(4-(imidazol-1-yl)phenyl)phenylsilane (4), [Bis(4-(imidazol-1-yl)phenyl)](4- bromophenyl)phenylsilane (5) and [Tri(4-(imidazol-1-yl)phenyl)](4-bromophenyl) silane (6) have been synthesized and characterized by FTIR, 1H NMR, 13C NMR and mass spectroscopy. They all display high thermal stability, are fluorescent with emission in the region of violet to blue, and possess large HOMO-LUMO energy gaps ranging from 4.9585 to 5.1879 eV, which could be potentially used as blue emitters or hole blocking materials in OLEDs. Moreover, the metal ion titrations based on Ag (I) and compounds 1-4 reveal that these ligands show distinguishable fluorescence response with increasing of Ag (I) ions.
- Wang, Dengxu,Niu, Yuzhong,Wang, Yike,Han, Jianjun,Feng, Shengyu
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experimental part
p. 2329 - 2337
(2010/10/05)
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- Building ultramicropores within organic polymers based on a thermosetting cyanate ester resin
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Ultramicropores with high surface areas (>530 m2 g -1) and narrow micropore size distribution (4-6 ) were engineered within a new cyanate ester resin, extending the microporous concept (20 ) to general thermosetting resins in the area of polymer chemistry.
- Zhang, Bufeng,Wang, Zhonggang
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supporting information; experimental part
p. 5027 - 5029
(2010/01/06)
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- Easily immobilized di- and tetraphosphine linkers: Rigid scaffolds that prevent interactions of metal complexes with oxide supports
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Di- and tetraphosphines with rigid phenyl-, biphenyl-, and tetraphenylstannane, -silane, and -methane scaffolds, and various substituents R, have been synthesized and immobilized via triethoxysilane-propagated formation of one or two surface-bound phospho
- Yang, Yuan,Beele, Bjoern,Bluemel, Janet
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p. 3771 - 3773
(2008/09/20)
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